Two boats sailing in close proximity may inevitably compare their boat speeds, perhaps even "race" each other. Over the last few centuries there have been numerous handicap systems designed to equalize the competitive chances of racing sailboats. Corollary to handicapping is another arcane art; that of scoring races. Scoring methods have both technical options, in part determined by handicap rules, as well as "human engineering" options in the sense that different solutions can work best for different constituencies, be they race organizers or sailors. Options may include single vs. multiple ratings, time on distance vs. time on time, pre/during/post-race handicapping, attempts to predict the environmental conditions on the race course, constructed courses, pursuit vs. staggered vs. fleet start racing, performance line and performance curve scoring. The underlying assumptions and motivations for these choices are presented along with the consequences of adopting them. The expectations of the competitors, and indeed their ability to intuitively grasp the fundamentals of how elapsed times are transformed into race rankings, are discussed with a view towards finding solutions that achieve a successful balance of fairness, transparency and acceptance.

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